SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives

C–C bond-forming carboxylation and cyclization of trimethyl­(2-methylenebut-3-yn-1-yl)­silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-fu...

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Veröffentlicht in:Organic letters 2015-11, Vol.17 (22), p.5706-5709
Hauptverfasser: Sekine, Kohei, Sadamitsu, Yuta, Yamada, Tohru
Format: Artikel
Sprache:eng
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Zusammenfassung:C–C bond-forming carboxylation and cyclization of trimethyl­(2-methylenebut-3-yn-1-yl)­silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the exo-olefin was that of a Z-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-exo-dig cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b03023